Nantucket may be best known for its cobblestone streets and weathered grey-shingled cottages, preppy rope bracelets, and a certain limerick about male onanism. But the island also distinguishes itself for being the only place in the U.S. that was effectively run by women, a kind of New England Amazonia.

Organizing our weekend around the history of women on the island gave our trip focus while forcing us to confront our limitations and dumb luck for being born into the lives we live, divisive political climate be damned.

It seemed like the perfect destination for a multi-gen trip this summer with my mother and 11-year-old daughter. The three of us were feeling especially bonded after a year of women’s marches and pussy-hat wearing, and agreed we wanted to go someplace that would be relaxing but also purposeful. With easy JetBlue flights from LaGuardia and no need to rent a car—it’s small enough to get around by bike, taxi, or shuttle—Nantucket also seemed manageable in scale both for older and much younger legs.

The island’s small size (it’s just 14 miles long, 3 to 5 miles wide) and isolation had a hand in shaping its early social structure. It was too sandy and windswept for serious agriculture, and so by the early nineteenth century, whaling had become Nantucket’s dominant industry. With their husbands gone for up to four years at a time, whaling wives became their family’s de facto leaders and chief breadwinners; some even gained unprecedented legal rights over property, a precursor of today’s power of attorney, while their husbands were away. (In the 1840s, women outnumbered men four to one.) Many opened businesses, and Centre Street between Main and Broad—now lined with boutiques like Patina, owned by jeweler Ted Muehling’s sister, and the gypset-cool CJ Laing—was known as Petticoat Row, because so many of the storefronts were owned and run by women. While no doubt their lives could be brutal and scrappy, many whaling wives not-so-secretly embraced their status. As a Nantucket Girls’ song from 1855 goes:

Then I’ll haste to wed a sailor, and send him off to sea,For a life of independence is a pleasant life for me…But when he says Goodbye my love, I’m off across the sea,First I’ll cry for his departure, then laugh because I’m free...

We tapped into some of this history at the Nantucket Whaling Museum at 13 Broad Street. In a converted warehouse, we sized up an 1847 spermaceti-candle forgery with a two-story wooden beam press and a 46–foot sperm whale skeleton plunging from the ceiling; we lingered by the museum’s impressive scrimshaw collection as well as portraits of notable Nantucketers, including Lydia Folger Fowler, MD, a local mid-nineteenth century physician and the second American woman to earn a medical degree. Frustrated by my mother’s glacial pace and insistence on reading every museum plaque (a pitfall of the multi-gen trip), my daughter Nell, who as a ‘tween is naturally drawn to the macabre, was finally reeled in by the Essex Gam (an archaic term for a conversation between whalers), a museum performer’s dramatic retelling of the ill-fated whale ship that sunk in 1820 in the Pacific after being attacked by a sperm whale, inspiring Herman Melville’s Moby Dick.

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By the early nineteenth century, whaling had become Nantucket’s dominant industry.

The other major factor in women’s influential status on the island was Quakerism. Established in Nantucket around 1708 in large part by the ministrations of Mary Coffin Starbuck and her husband, who ran a trading post and meeting house (she could read and write; her husband was illiterate), Quakerism asserted that God spoke to everyone—that is, everyone was equal. It eventually became the dominant religion of Nantucket’s ruling elite. During the week, you can visit the 1838 Quaker meeting house at 7 Fair Street—though not the original that was run out of Starbuck’s home, the building retains a lovely austere minimalism, with hand-hewn wooden benches and plain walls. (We learned that Quakerism’s egalitarianism had an affect off the island, too, as Nantucket daughter and Quaker Lucretia Coffin Mott, also an abolitionist and women’s rights supporter, joined suffragist Elizabeth Cady Stanton in July 1848 to establish the first Women’s Rights Convention at Seneca Falls, New York.)

You can’t talk about women’s history on Nantucket without a hat tip to Maria Mitchell, America’s first professional female astronomer, who achieved notoriety for using a telescope to discover a comet (later named for her) in 1847. Her Quaker parents valued education, and when she was 12, she helped her father, a bank officer with a side gig as a maritime chronometer setter, calculate the exact moment of an annular eclipse. (She would later go on to teach astronomy at Vassar.) The Maria Mitchell House at 1 Vesey Street, where she lived until she was 18, is a surprisingly moving collision of the domestic and scientific, with its 1828 kitchen lined with crockery and original island-style paint-splattered floor (my daughter loved the attic full of children’s playthings, like a doll-size tea set and furniture), and Mitchell’s brass telescope standing in a floral-papered sitting room, where the grandfather clock continues to tick. The Association also runs an observatory and small Natural Science Museum next door, full of taxidermied local animals, bones, and shells.

On today’s Nantucket, women are arguably making their greatest mark on the food scene. At the urging of Joy Margolis—who with her husband Greg runs the newish Nantucket Culinary Center in town and is tapped into the island’s foodways—we swung by Moors End Farm a few miles out of town at 40 Polpis Road. Abby Slosek’s grandfather bought the land in 1958, and today, she works it with her family. Slosek has managed to get the island’s sandy soil to yield the plumpest red tomatoes, squash, peppers, and practically every type of leafy green, and runs both a farm stand out of the driveway and the island’s first CSA. Six months pregnant and wearing cargo shorts and a blond ponytail, Slosek was happy to walk us around her fields, urging my daughter to taste a freshly picked bean or strawberry and showing off her mobile coop containing plucky Rhode Island Red chickens, which she moves between rows so the birds can keep the bugs down and fertilize along the way.

One beneficiary of Slosek’s harvest is the Club Car Restaurant, a Main Street mainstay named for the 1800s rail car that houses the bar. The restaurant reopened early this summer after its first renovation in 40 years with chef Mayumi Hattori and GM Tanya McDonough (veterans of other island restaurants) at the helm, in a contemporary dining room awash in blues and bathed in the most flattering golden light. I hadn’t expected to eat anything more on the island than lobster rolls and clam chowder. But Hattori, babyfaced and wearing a top-knotted head scarf, turns out impossibly fresh and elevated Cal-Mediterranean cuisine that draws equally, too, on her Japanese and Spanish heritage: think grilled whole black bass stuffed with pea tendrils, chickpeas, roasted tomatoes and hawaj (a turmeric clove spice); or the succulent rabbit al ajillo, her grandmother’s recipe cooked with amontillado and herbs. I would have stayed for another drink in train car, the closest thing Nantucket may have to a scene thanks to the live piano sing-along every night, but my mom and daughter were both too tired.

Of course, it wasn’t all history lessons—we took out bikes and pedaled several miles around the island on protected bike trails; hit the scenic Brant Point lighthouse and Jetties beach; tried on vintage Lily Pulitzer dresses at Current Vintage; and hung by the pool at White Elephant Village, where my daughter practiced handstands, my mother read The New Yorker, and I drank a glass of wine and scrolled through Instagram.

Organizing our weekend around the history of women on the island gave our trip focus while forcing us to confront our limitations and dumb luck for being born into the lives we live, divisive political climate be damned. “You would have made the worst whaling wife,” Nell told me at the museum when our docent described the long, bitter winters in which women held down every role: mother, head of household, handywoman, breadwinner (mainly, she knows how much I despise the cold). So much for modeling empowerment. Unexpectedly, though, we were all modeling other roles. Nell got to see me as a daughter—witnessing flashes of my grumpy and petulant teenage self, or my mother brushing loose strands of hair out of my face. And my mother got to watch me mothering my daughter—helping her tearily remount her bike after she skidded on a patch of sand, nagging her to pick up her wet towels. These reflections and distortions seemed to connect us to a long, long line of mothers and daughters whose lives were admittedly more about survival than recreation—but who surely felt, at the end of the day, a similar comfort in the easy company of women.

Getting Around

The island is ideal for cyclists, with more than 29 miles of bike paths and cyclist-friendly roadways, though fair warning: The town’s cobblestones do get very bumpy. You can rent at Young’s Bicycle Shop in town, though many hotels—including the White Elephant and its sister resort hotel, White Elephant Village—have a fleet you can take out for free.

Eating and Drinking

Breakfast at the White Elephant (with delicious lobster eggs Benedict and cold-pressed juices) is a must. Or head over to Black-Eyed Susan’s at 10 India Street, a diner-style island institution opened by Susan Handy and Jack Worster (it closes at 1 p.m. and reopens again for dinner at 6, from April to the end of October). Try the Pennsylvania Dutch pancakes with Jarlsberg, which arrives with crispy edges, gooey insides, and a side of super thin bacon.

The Nantucket Culinary Center has a little café with grain salads and sandwiches. Out of their gleaming new test kitchen, Joy and Greg Margolis run classes and workshops that are open to the public; we dropped in on a canning class.

At the Club Car Restaurant, Chef Mayumi Hattori serves up elevated Cal-Medi cuisine that feels like Venice Beach meets Ottolenghi, with veggies at the center, plenty of seafood, and responsibly sourced meat. It can get very crowded, so book ahead.

And you won’t want to miss sundowners at the Wauwinet, a historic hotel on the east side of the island with a sweeping lawn and view of the bay (in summer you can take an hour-long water taxi from the White Elephant, but they also run regular shuttles from town if you don’t have a car). Stay for dinner in the genteel dining room for global takes on local ingredients, like the butter-poached lobster with "forbidden" rice and pickled coconut, and lamb with summer beans.

If you don’t have a kid with you, aim for a night cap at Greydon House, a boutique hotel in town whose intimate, wood-paneled bar is cleverly decorated by Roman and Williams to resemble a captain’s quarters on a boat.

History Lessons

Nantucket Whaling Museum: Open daily from late May to late October from 10 a.m. to 5 p.m., with shorter hours during the off-season.

Quaker Meeting House: While not often open to the public, the building is included in the two tours of Quakerism on Nantucket that leave twice daily from the Whaling Musuem. Or, you could try dropping by the Nantucket Historical Society’s Research Library on Monday, Tuesday, Thursday, or Friday from 1-4 p.m. and ask to be let in.

Maria Mitchell House: There are hourly tours from Monday to Saturday, 10 a.m. to 4 p.m. The neighboring Science Museum and Shop keep the same hours.

Background Reading

I picked up a copy of * The Daring Daughters of Nantucket Island * by Jascin Leonardo Finger at the Maria Mitchell House. I found it to be a surprisingly accessible and engaging book with a focus on Quakerism on the island.